Experts: 4 Questions To Ask To Figure Out Whether You’ll Be Happy at a New Job

cheerful man in glasses shaking hands with recruiter on job interview.
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It’s a great time to look for a new job. There are nearly twice as many open positions as there are job seekers. Employers are scrambling to fill head counts and retain the workers they do have, and prospective hires are now in positions where they can afford to be more choosy. 

It’s truly a candidate’s market. Here are four top questions our experts suggest you come prepared with.

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While employees jump ship into the “Great Resignation,” seeking opportunities for more rewarding work and better pay, many of them — younger workers in particular — are finding that the supposedly greener pastures weren’t what they expected. 

According to a recent survey by The Muse, 72% of millennial and Gen Z job seekers said they felt surprise or regret that a new job was very different from what they were led to believe. 

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Recruiters and hiring managers may be a part of the problem. Short-staffed themselves and desperate to fill vacant roles, proper due diligence may be giving way to a crisis approach of hire now, evaluate later. 

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Remote work and hiring also can make it hard to get a sense of what a job is really like, as it has become more common than ever to sign on without having ever stepped foot in a company’s office or met anyone face to face. What’s more, remote work tends to create a void of office culture, and that has serious consequences for an employee’s sense of well-being, says Dr. Shonna Waters, vice president of strategic alliances and partnerships for BetterUp.

“With the rise of remote work,” Waters said, “it’s more difficult to form a sense of belonging with co-workers and fully participate in company culture.”

She added that the importance of that culture — which represents the shared values, attitudes, behaviors and standards that make up a work environment — shouldn’t be underestimated in its impact on the day-to-day experience. 

According to BetterUp’s recent report, “Connection Crisis: Why Community Matters in the New World of Work,” 43% of employees say their organization isn’t doing enough to help them feel a sense of connection. They also found that employees who have few friends at work have a 61% higher likelihood of seriously job-seeking outside their organization. 

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“That’s a big problem and perhaps a reason why we’re seeing the workforce exploring new employment opportunities at such high rates,” Waters said. 

So how can a job seeker head off that surprise and regret before it hits? Experts say the questions you ask a potential employer in an interview are key. Good questions not only help you stand out from the crowd, but the answers you get provide a signal when it comes to figuring out whether you’ll really be happy. 

1. What Kind of Financial Wellness Benefits Do You Offer? 

Mindy Yu, director of investing for Betterment at Work, says it’s important for job seekers — especially recent graduates — to consider the value of the job beyond the salary or signing bonus.

“Pay attention to the financial wellness benefits in your compensation package and make the most out of them,” she said.

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This includes their matching contribution to your 401(k), any wellness stipends, flexible spending accounts (FSA) or health savings accounts (HSA) and employer-sponsored emergency funds. 

For recent grads or younger workers, Yu also says it’s worth asking about student loan management solutions. Some employers may offer programs for financial and debt repayment advice, or even contributions to a student loan matching program. 

“While they might seem like a small amount compared to the salary,” Yu said, “these benefits can’t be underestimated when (people are) considering setting themselves up for long-term financial success.” 

2. What Does Your Company Do To Foster Belonging? 

A strong culture of connection will make your work experience more fulfilling. Waters says high rates of belonging have been linked to higher job performance, increased ability to innovate and make clear decisions and improved overall mental health.

On the flip side, isolation at work is likely to lead to more stress, burnout, anxiety and depression.

“Job seekers should want to hear from the people they’re interviewing with that the company is flexible in workers’ specific needs as realistically as possible,” Waters said, “(and) that team leaders are creating space for employee connections and that there’s a plan to immerse new hires in this culture so they can foster strong feelings of connection and be set up for success.”

3. How Will My Success Be Measured?

It’s important to understand going into a new job how employees are evaluated and rewarded in order to make sure that their expectations sound clear and reasonable, Waters says. 

Related or follow-up questions could include things like, “What do you expect the person in this role to accomplish in their first 90 days?” This not only shows that you’re results-oriented, but prompts details around what they’ll immediately expect of you.

Candidates might also ask interviewers what their most successful employees do differently.

“This will show the hiring manager that you’re thinking outside of the box,” Waters said, “but also give you a good sense of what qualities they value and ultimately reward.” 

4. What Are You Excited To Be Working on Right Now? 

To get past the carefully crafted job description and lists of benefits, seeking out personal anecdotes from your interviewer is a good way to get a better sense of what the day-to-day might really be like, Waters says. She also suggests raising questions about the management style of the team lead to get a sense of whether it aligns with how you like to work. 

“Many employees now value health and wellbeing over financial compensation,” Waters said, “so candidates may want to ensure that the work environment, expectations and benefits are a good fit for their broader priorities in life.”

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